Vacation rentals in Cow Key Channel

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Top-rated vacation rentals in Cow Key Channel

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A welcoming porch area is presented, featuring a light blue exterior and white railings. Two chairs are set beside the entrance, which includes a round window and a decorative welcome mat. Lush greenery enhances the inviting space.

Home in Key West

5 out of 5 average rating, 11 reviews

Key Lime Retreat

Weekly Treat! Downtown vacation experience for entire family. Located in the hearth of Historic Seaport location in Key West. Conveniently walking distance to Duval St shopping, offices, entertainment, restaurants, bars, and everything Key West has to offer. There is not much to say about this condo, The location talks for itself! It’s a must have Key West experience on a quite gated community just steps away from Duval St. It’s a true Gem to experience the Key West living to the fullest extend.

Guest favorite

A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.

Home in Cudjoe Key

4.83 out of 5 average rating, 30 reviews

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below March 30th - April 15th, 2025 April 23rd - May 3rd, 2025 May 17th - May 31st, 2025 June 6th - June 13th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Superhost

A view of the oceanfront community features modern two-story buildings with white exteriors and metal roofs. Palm trees provide greenery amongst the paved pathways. The blue sky is filled with fluffy clouds, creating a bright and welcoming atmosphere.

Apartment in Marathon

5 out of 5 average rating, 4 reviews

Ocean Side Paradise Awaits!

This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic Ocean. Take advantage of the many tiki huts, fishing dock, air-conditioned clubhouse, and grilling station to cook up your fresh catch. Our turnkey townhouse is perfect for a short vacation or a longer-term stay. Everything in the complex, from the facilities to the furnishings, is brand new. Don't miss the opportunity to experience paradise at its finest. Book your stay now!

Top guest favorite

An outdoor deck is visible along the canal, featuring a picnic table and two sun loungers. A kayak in bright orange and white rests on the surface. The sky is clear, with a few clouds, and a calm waterway is seen in the background.

Cottage in Marathon

4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

Superhost

A community pool area is depicted, featuring a clear blue pool surrounded by a sun deck. Lounge chairs are positioned nearby, and colorful Adirondack chairs line the railing, providing a view over the water under a bright blue sky with scattered clouds.

Home in Cudjoe Key

4.91 out of 5 average rating, 110 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Guest favorite

A heated pool is framed by two thatched umbrellas, offering shade and relaxation. Surrounding the pool are several wooden lounge chairs, inviting comfort in the sun. Lush greenery is visible in the background, enhancing the serene ambiance of the outdoor space.

Home in Marathon

5 out of 5 average rating, 33 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Superhost

A serene waterfront scene features calm turquoise waters with gentle waves. A thatched-roof gazebo extends over the water's edge, providing a shaded area. In the background, a row of palm trees sways slightly under the bright blue sky, adding to the tranquil atmosphere.

Cottage in Cudjoe Key

4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Guest favorite

A waterfront patio area features a white railing overlooking clear turquoise waters. Planted pots with greenery are positioned on either side of a small grill. The serene view extends to the horizon, with boats visible in the distance.

Home in Cudjoe Key

4.89 out of 5 average rating, 104 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Superhost

Home in Marathon

5 out of 5 average rating, 5 reviews

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Guest favorite

A bright and airy living area is filled with natural light from large windows offering expansive water views. A comfortable light blue sofa and a matching armchair provide seating. A decorative coffee table sits in the center, and tropical plants are visible outside.

Townhouse in Key West

5 out of 5 average rating, 8 reviews

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

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What guests are saying

Huge Swim Spa~ Incredible Special Fall Pricing

5 out of 5 average rating, 5 reviews1 month ago

We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.

Home in Key Colony Beach

What guests are saying

(#8)Waterfront 4 Bed 3 Bath Pool Home w Free Dock

4.85 out of 5 average rating, 26 reviews2 months ago

We had a delightful time. The unit was clean & comfortable and easily accommodated our party of 5 adults. The balcony was very pleasant and had a great relaxing view. The shared beach was also very relaxing with plenty of chairs and a nice covered card table area. This is in addition to the multiple seating options at our private pool. Families were enjoying the provided kayaks of which there were plenty. Susan and Dale were extremely responsive to all of our inquiries including showing up to address an issue within 15 minutes! Overall we had a very pleasant stay.

Home in Marathon

What guests are saying

Gone Coastal 2

4.92 out of 5 average rating, 53 reviews2 weeks ago

My family and I loved our trip to Key West. This was our first time booking through Airbnb. We were so happy we went with Chris place. It was clean, spacious and comfortable. We would definitely stay here again. We loved sitting on the balcony and enjoy our morning coffee. It was just so very peaceful. I would highly recommend this property.

Home in Key West

What guests are saying

Reel Island Retreat #273 Venture Out in the Keys

4.8 out of 5 average rating, 5 reviews1 month ago

Location, location, location!!! Fishing was a breeze, minutes to deep water fishing. Smooth check-in, parking was easy with plenty of over flow parking even with a boat trailer and extra vehicle. The park is lively with plenty of activities and friendly people. Lots of restaurants and bars close by and Key West is an Uber ride away! Great vacation in a perfect location!

Home in Cudjoe Key

What guests are saying

Luxury Waterfront Retreat with Dockage & Pool

4.8 out of 5 average rating, 35 reviews2 weeks ago

We enjoyed our stay. The home was comfortable and very clean. It was nice to have a view of the water and a heated pool! The rooms were comfortable and accommodating for our family. Naomi was quick to respond when we had questions. I would stay here again! This spot was close to many restaurants, grocery stores, and right on bike paths!

Home in Marathon

What guests are saying

Waterfront Oasis3/2 Direct Ocean

5 out of 5 average rating, 3 reviews9 months ago

Beautiful views and great spaces! We’ve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldn’t get enough of all the beautiful views from sunrise to sunset whether it was on the porch, in the pool, or out by the Tiki Hut. Every bedroom has water views as well. Boat access was an easy out to snorkeling, diving, fishing, or whatever you like to do. There are two kayaks for use, which made for some nice outings to explore the immediate area. The kitchen had everything needed for cooking, and even had an extra under-the-counter ice machine. We had a great time here, and would stay again. Thank you to the owners for sharing your property.

Home in Marathon